68435-07-4Relevant academic research and scientific papers
ADAMANTANYL-SUBSTITUTED BENZAMIDE COMPOUNDS AND THEIR USE AS P2X7 RECEPTOR ANTAGONISTS
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Page/Page column 20-21; 25, (2020/03/15)
The present invention relates to adamantanyl-substituted benzamide compounds and their use as antagonists of the P2X7 purinoreceptor. The invention further relates to methods for the treatment of disease and conditions associated with the P2X7 purinoreceptor.
MONOMER, POLYMER, RESIST COMPOSITION, AND PATTERNING PROCESS
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Paragraph 0381-0385, (2019/06/19)
The present invention provides a polymerizable monomer containing a substituent whose polarity is changed by action of acid, a polymer containing a substituent whose polarity is changed by action of acid, a resist material containing the polymer as a base
Pharmacological Evaluation of Novel Bioisosteres of an Adamantanyl Benzamide P2X7 Receptor Antagonist
Wilkinson, Shane M.,Barron, Melissa L.,O'Brien-Brown, James,Janssen, Bieneke,Stokes, Leanne,Werry, Eryn L.,Chishty, Mansoor,Skarratt, Kristen K.,Ong, Jennifer A.,Hibbs, David E.,Vugts, Danielle J.,Fuller, Stephen,Windhorst, Albert D.,Kassiou, Michael
, p. 2374 - 2380 (2017/11/21)
Adamantanyl benzamide 1 was identified as a potent P2X7R antagonist but failed to progress further due to poor metabolic stability. We describe the synthesis and SAR of a series of bioisosteres of benzamide 1 to explore improvements in the pharmacological properties of this lead. Initial efforts investigated a series of heteroaromatic bioisosteres, which demonstrated improved physicochemical properties but reduced P2X7R antagonism. Installation of bioisosteric fluorine on the adamantane bridgeheads was well tolerated and led to a series of bioisosteres with improved physicochemical properties and metabolic stability. Trifluorinated benzamide 34 demonstrated optimal physicochemical parameters, superior metabolic stability (ten times longer than lead benzamide 1), and an improved physicokinetic profile and proved effective in the presence of several known P2X7R polymorphisms.
Interaction between an amantadine analogue and the transmembrane portion of the influenza A M2 protein in liposomes probed by 1H NMR spectroscopy of the ligand
Kolocouris, Antonios,Hansen, Raino K.,Broadhurst, R. William
, p. 4975 - 4978 (2007/10/03)
1H NMR spectroscopy of a fluoroamantadine ligand was used to probe the pH dependence of binding to the transmembrane peptide fragment of the influenza A M2 proton channel (M2TM) incorporated into 1,2-dimyristoyl-sn- glycero-3-phosphocholine liposomes. Above pH 7.5, when M2TM bound the ligand, fluoroamantadine resonances became too broad to be detected. Fluoroamantadine interacted weakly with the liposomes, indicating it may first bind to the bilayer and then block target channels after diffusion across the membrane surface.
POLYMERIZABLE ADAMANTANE DERIVATIVES AND PROCESS FOR PRODUCING THE SAME
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, (2008/06/13)
A compound shown by the following formula: ???wherein each of R1a, R2a, R3aand R4arepresents a substituent selected from a non-reactive atom, a non-reactive group, a hydroxyl group and an amino group, and at least two members selected from R1a, R2a, R3aand R4aare a hydroxyl group, a carboxyl group or an amino group; is subjected to an esterification reaction or an amidation reaction with a polymerizable unsaturated compound (e.g., an alcohol, a carboxylic acid, an amine) in the presence of a catalyst comprising an element selected from the Group 3 elements, such as a samarium compound, to obtain a polymerizable adamantane derivative having at least one polymerizable unsaturated group in high yield.
BENZAMIDINE DERIVATIVES SUBSTITUTED BY CYCLIC AMINO ACID AND CYCLIC HYDROXY ACID DERIVATIVES AND THEIR USE AS ANTI-COAGULANTS
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, (2008/06/13)
This invention is directed to benzamidine derivatives substituted by cyclic amino acid and cyclic hydroxy acid derivatives which are useful as anti-coagulants. This invention is also directed to pharmaceutical compositions containing the compounds of the invention, and methods of using the compounds to treat disease-states characterized by thrombotic activity.
Site selective oxidation of tricyclo3,7>decane (adamantane) and some of its derivatives using fungi of the genus Absidia
Ridyard, Colin H.,Whittaker, Roger A.,Higgins, Stanley D.,Roberts, Stanley M.,Willets, Andrew J.,et al.
, p. 1811 - 1820 (2007/10/03)
Tricyclo3,7>decane 1a has been converted into 1-hydroxytricyclo3,7>decane 1b, tricyclo3,7>decane-1,4ax-diol 4b, tricyclo3,7>decane-1,3-diol 3b and to a lesser extent, 2-hydroxytricyclo3,7>decane 4a (20 to 40percent overall yield) using the microorganisms Absidia glauca (IMI 239693), A. cylindrospora (IMI 342950), A. spinosa (IMI 193887), A. spinosa var. biappendiculata (IMI 238610) and A. cylindrospora var. nigra (IMI 240053) as biocatalysts.In addition, A. cylindrospora (IMI 342950) converted tricyclo3,7>decane-1-carboxylic acid 1c into 4ax-hydroxytricyclo3,7>decane-1-carboxylic acid 4c with almost complete regioselectivity.Tricyclo3,7>decane derivatives 1d-g were used as biohydroxylation substrates with A. cylindrospora (IMI 342950), giving selective biohydroxylation at the 4ax- and/or the 3-position.The 4ax-selectivity was confirmed by X-ray crystal structure determinations of 4b, 4c and 4j.
Selective biohydroxylation of 1-substituted adamantanes using Absidia cylindrospora (I.M.I. 342950)
Bailey, Patrick D.,Higgins, Stanley D.,Ridyard, Colin H.,Roberts, Stanley M.,Rosair, Georgina M.,Whittaker, Roger A.,Willetts, Andrew J.
, p. 1833 - 1834 (2007/10/03)
The biohydroxylation of 1-substituted adamantanes using Absidia cylindrospora in a whole-cell oxidation system exclusively generated 3-hydroxy and 4ax-hydroxy derivatives; the assignments were confirmed by three X-ray crystal structure determinations.
Transmission of Polar Substituent Effects in Saturated Systems: Synthesis and 19F NMR Study of 3-Substituted Adamant-1-yl Fluorides
Adcock, William,Kok, Gaik B.
, p. 356 - 364 (2007/10/02)
An extensive series of 3-substituted adamant-1-yl fluorides (3) covering a diverse range of substituents has been synthesized and characterized and the 19F chemical shifts measured.By use of multiple linear regression analysis, it is revealed that there i
